Synthesis of Quinolines, 2-Quinolones, Phenanthridines, and 6(5<i>H</i>)-Phenanthridinones via Palladium[0]-Mediated Ullmann Cross-Coupling of 1-Bromo-2-nitroarenes with β-Halo-enals, -enones, or -esters

Banwell, Martin G.; Lupton, David W.; Ma, Xinghua; Renner, Jens; Sydnes, Magne O.

doi:10.1021/ol0490375

Cited by 126 publications

(57 citation statements)

References 34 publications

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“…As an alternative, one pot system for imine synthesis has been under investigations, such as Rh 6 (CO) 16 [29], PdCl 2 (PPh 3 ) 2 /SnCl 2 /CO [30], Pd/C/H 2 [31], and Ru 3 (CO) 12 /CO [32]. However, these protocols required transition-metal catalysts, elevated pressures, high temperatures, which made them far from ideal for laboratory-scale synthetic chemistry.…”

Section: Introductionmentioning

confidence: 99%

One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst

Zheng

et al. 2008

Catal Lett

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We have successfully prepared a novel Ni/SiO 2 magnetic catalyst, and put it into the process of one pot synthesis of imines directly from aromatic nitro compounds and aldehydes for the first time. The catalyst has been characterized by XRD, IR, TEM, SEM, TPR, H 2 -TPD and XPS. The prominent merits of the Ni/SiO 2 magnetic catalyst passivated with a gas mixture are that it can be stored safely in air below 423 K and needs no activation before use. In the catalytic test, most conversion and selectivity is almost up to 100%, and it is found that the catalyst is highly efficient, stable, and reusable for the synthesis of imines.

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Section: Introductionmentioning

confidence: 99%

One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst

Zheng

et al. 2008

Catal Lett

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“…44 Porém, de forma mais abrangente, a investigação de métodos com catálise por sais de paládio levou ao desenvolvimento de novas metodologias e abordagens para a síntese de derivados de 1. Os pesquisadores Ames e Opalko foram os primeiros a relatar a síntese de 1 por reações de desidro-halogenação de 2-halobenzoilanilinas ou de benzoil-2-haloanilinas catalisadas por paládio (Figura 2, C).…”

Section: Introductionunclassified

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

Costa¹,

Silva²,

Lucas³

et al. 2016

Química Nova

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publicado na web em 18/02/2015 SYNTHESIS OF PHENANTHRIDINONE DERIVATIVES BY DIRECT ARYLATION. CHARACTERIZATION OF THE ABSORPTION AND EMISSION SPECTRA FOR REPRESENTATIVE EXAMPLES. The phenanthridinone heterocyclic system has attracted considerable attention in recent years due to the diverse array of physical, chemical and pharmacological properties demonstrated by natural and synthetic derivatives. As a consequence there has been considerable development of synthetic methodology for the synthesis of this and related heterocyclic ring systems. The synthetic literature is discussed and is compared with a direct arylation methodology for the intramolecular cyclization of tertiary (2-iodo)benzoylamides to generate the biaryl bond of these compounds. The efficient methodology allowed the synthesis of a number of previously unknown phenanthridinone products. The photoluminescent properties of representative examples were characterized and it is proposed that the previously unknown compound 1s reveals dual fluorescence in a manner similar to the known compound 1r.

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“…Although several synthetic routes to substituted phenanthridines have been reported, most of them require multi-step synthesis, strict anhydrous conditions, poor yields or metal catalysts. [6][7][8][9][10] Thus, there is a need for more efficient, versatile and simpler synthetic methods of creating phenanthridines.…”

Section: Introductionmentioning

confidence: 99%

Ammonium Acetate: An Efficient Reagent for the One-pot Synthesis of 5-Aryl-7,8,13,14-tetrahydrodibenzo[a,i] phenanthridines, 2,4-Diaryl-6,7-benzo-3-azabicyclo[3.3.1]nonan-9-ones and α,α'-Bis(substituted benzylidene)cycloalkanones

2009

Bulletin of the Korean Chemical Society

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The condensation of cyclic ketone with aromatic aldehydes in the presence of ammonium acetate under ethanol media affords the corresponding 5-aryl-7,8,13,14-tetrahydrodibenzo[a,i]phenanthridine with excellent yield. This mild and efficient procedure with high yield is also applied to the synthesis of 2,4-diaryl-6,7-benzo-3-azabicyclo-[3.3.1]nonan-9-ones and α,α'-bis(substituted benzylidene)cycloalkanones.

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Synthesis of Quinolines, 2-Quinolones, Phenanthridines, and 6(5H)-Phenanthridinones via Palladium[0]-Mediated Ullmann Cross-Coupling of 1-Bromo-2-nitroarenes with β-Halo-enals, -enones, or -esters

Cited by 126 publications

References 34 publications

One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst

One Pot Synthesis of Imines from Aromatic Nitro Compounds with a Novel Ni/SiO2 Magnetic Catalyst

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

Ammonium Acetate: An Efficient Reagent for the One-pot Synthesis of 5-Aryl-7,8,13,14-tetrahydrodibenzo[a,i] phenanthridines, 2,4-Diaryl-6,7-benzo-3-azabicyclo[3.3.1]nonan-9-ones and α,α'-Bis(substituted benzylidene)cycloalkanones

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